1,3-Dioxacyclopentanes, their pesticidal use and compositions for pesticidal use

ABSTRACT

Substituted aminoketals of the formula   &lt;IMAGE&gt;   in which R1 to R4 are various organic radicals and R2 may also be hydrogen, are fungicidally active. Some of the compounds are new.

The present invention relates to the use of substituted aminoketals,some of which are known, as pest-combating agents.

It has already been disclosed that certain aminoketals, such as, forexample,2-methyl-2-(3,4,5-trimethoxyphenyl)-4-(pyrrolidin-1-ylmethyl)-1,3-dioxolane,2-cyclohexyl-2-phenyl-4-(morpholin-1-ylmethyl)-1,3-dioxolane,2-phenyl-2-chloromethyl-4-(morpholin-1-ylmethyl)-1,3-dioxolane and2-methyl-2-(4-methyl-but-3-en-1-yl)-4-(piperidin-1-ylmethyl)-1,3-dioxolane,exhibit an action, for example as diuretics or hypotensive agents, inthe pharmaceuticals sector [see, for example, French PatentSpecification No. 2,163,322; Japanese Patent Application No. 52-33,608;Belgian Patent Specification No. 776,421; Dutch Patent Specification No.6,609,579; U.S. Pat. No. 3,337,408 and U.S.S.R. Patent Specification No.722,910; and also A. R. Patel et al., "J. Pharm. Sci. 52 (1963), No. 6,page 588-592; J. Wolinski et al., "Acta Pol. Pharm. 1980, 37 (1), pages15-24 (Polish), 1978, 35 (6), pages 621-627 (Polish), 1978, 35 (3),pages 265-272 (Polish) and 1977, 34 (2), pages 143-147 (Polish)].

Furthermore, aminoketals, such as, for example,2,2-dimethyl-4-(morpholin-1-ylmethyl)-1,3-dioxolane, are known asintermediate products or starting materials for the preparation of otherpharmaceutically active compounds [see, for example, N. D. Harris, "J.Org. Chem. 28 (1963), No. 3, pages 745-748 and Karpysow "Bio-Org. Khim"1979, 5 (2), pages 238-241 (Russian)]. None of the known aminoketals areknown to have an action in the field of plant protection.

Furthermore, it has already been disclosed that aminopropiophenonederivatives, such as, for example, 4-tert.-butylphenyl1-dimethylamino-prop-2-yl ketone (see DE-OS [German PublishedSpecification] No. 3,019,497), as well as organic sulphur compounds,such as, for example, zinc ethylene-1,2-bis-(dithiocarbamate) (see R.Wegler, "Chemie der Pflanzenschutz- und Sch/a/ dlingsbek/a/mpfungsmittel" [Chemistry of Plant Protection Agents and Pest-combatingAgents], Springer Verlag Berlin 1970, Volume 2, page 65 et seq.),possess fungicidal properties. However, the action of these compounds isnot always completely satisfactory in some fields of use, in particularwhen low amounts and concentrations are used.

It has been found that substituted aminoketals, some of which are known,of the formula (I) ##STR2## in which R¹ represents optionallysubstituted alkyl, or represents alkenyl and alkinyl, or optionallysubstituted cycloalkyl, optionally substituted aralkenyl or optionallysubstituted aryl,

R² has the same meaning as R¹ and furthermore represents hydrogen,

R³ represents alkyl, alkenyl, alkinyl, optionally substitutedcycloalkyl, optionally substituted aryl or optionally substitutedaralkyl,

R⁴ represents alkyl, alkenyl, alkinyl, optionally substitutedcycloalkyl, optionally substituted aryl or optionally substitutedaralkyl, or

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent an optionally substituted heterocyclic structure which cancontain further hetero-atoms,

and their physiologically tolerated acid addition salts and metal saltcomplexes, have fungicidal properties.

The compounds of the formula (I) can occur as geometric isomers orisomer mixtures of different compositions. The pure isomers as well asthe isomer mixtures are claimed according to the invention.

Surprisingly, the substituted aminoketals of the formula (I) to be usedin accordance with the invention exhibit a more pronounced fungicidalaction than the compounds known from the prior art, namely4-tert.-butylphenyl 1-dimethylaminoprop-2-yl ketone and zincethylene-1,2-bis-(dithiocarbamate), which are compounds having the samedirection of action. The substances according to the invention thusrepresent an enrichment of the art.

Formula (I) gives a general definition of the substituted aminoketals tobe used in accordance with the invention. Preferred compounds are thosein which

R¹ represents straight-chain or branched alkyl having 1 to 18 carbonatoms; substituted alkyl, such as straight-chain or branchedhalogenoalkyl having 1 to 12 carbon atoms and 1 to 5 halogen atoms,straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in thealkyl part, aralkyl, aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphinylalkyl and arylsulphonylalkyl, each having 1 to 6 carbonatoms in each alkyl part and 6 to 10 carbon atoms in the aryl part, theradicals in each case being optionally monosubstituted orpolysubstituted by identical or different substituents, the followingbeing suitable aryl substituents in each case: halogen, cyano, nitro;alkyl, alkoxy and alkylthio, each having 1 to 4 carbon atoms;halogenoalkyl, halogenoalkoxy, halogenoalkylthio, each having 1 or 2carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, andphenoxy or phenyl which is optionally substituted by halogen, inparticular fluorine or chlorine, or by alkyl having 1 to 4 carbon atoms;and represents cycloalkylalkyl having 1 to 4 carbon atoms in the alkylpart and 3 to 7 carbon atoms in the cycloalkyl part which is optionallymonosubstituted or polysubstituted by alkyl having 1 to 4 carbon atoms,and also represents straight-chain or branched alkenyl or alkinyl, eachhaving 2 to 6 carbon atoms, cycloalkyl which has 3 to 7 carbon atoms andis optionally monosubstituted or polysubstituted by identical ordifferent alkyl radicals having 1 to 4 carbon atoms, or represents arylhaving 6 to 10 carbon atoms and arylalkenyl having 2 to 6 carbon atomsin the alkenyl part and 6 to 10 carbon atoms in the aryl part, each ofwhich is optionally monosubstituted or polysubstituted by identical ordifferent substituents, suitable aryl substituents in each case being:halogen, cyano, nitro; alkyl, alkoxy, alkylthio, each having 1 to 4carbon atoms; halogenoalkyl, halogenoalkoxy, halogenoalkylthio, eachhaving 1 to 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5to 7 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in thealkyl part, and phenoxy or phenyl which is optionally substituted byhalogen, in particular fluorine or chlorine, or by alkyl having 1 to 4carbon atoms;

R² has the same meaning as R¹ and may be identical or different to thisradical, and additionally represents hydrogen,

R³ represents straight-chain or branched alkyl having 1 to 12 carbonatoms, straight-chain or branched alkenyl having 3 to 12 carbon atoms,straight-chain or branched alkinyl having 3 to 7 carbon atoms,cycloalkyl which has 5 to 7 carbon atoms and is optionallymonosubstituted or polysubstituted by identical or different alkylgroups having 1 to 4 carbon atoms, and aryl having 6 to 10 carbon atomsor aralkyl having 1 or 2 carbon atoms in the aryl part, each of whichradicals is optionally monosubstituted or polysubstituted by identicalor different substituents, suitable aryl substituents in each casebeing:

halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1 or2 carbon atoms and 1 to 5 halogen atoms;

R⁴ represents straight-chain or branched alkyl having 1 to 12 carbonatoms, straight-chain or branched alkenyl having 3 to 12 carbon atoms,straight-chain or branched alkinyl having 3 to 7 carbon atoms,cycloalkyl which has 5 to 7 carbon atoms and is optionallymonosubstituted or polysubstituted by identical or different alkylgroups having 1 to 4 carbon atoms, and aryl having 6 to 10 carbon atomsor aralkyl having 1 to 2 carbon atoms in the alkyl part and 6 to 10carbon atoms in the aryl part, each of which radicals is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, suitable aryl substituents in each case being;

halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1 or2 carbon atoms and 1 to 5 halogen atoms; or

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent a 5-membered to 7-membered, saturated or unsaturatedheterocyclic structure, which has 1 to 3 heteroatoms, preferablynitrogen or oxygen, and is optionally monosubstituted or polysubstitutedby identical or different substituents, the following being preferablymentioned as substituents: alkyl having 1 to 4 carbon atoms,alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part and phenyl.

Particularly preferred substituted aminoketals of the formula (I) arethose in which

R¹ represents straight-chain or branched alkyl having 1 to 12 carbonatoms, cyclopropyl, cyclopentyl, cyclohexyl, straight-chain or branchedhalogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, orphenyl, phenylalkyl, phenoxyalkyl, benzyloxyalkyl, phenylthioalkyl,phenylsulphinylalkyl and phenylsulphonylalkyl, each having 1 to 5 carbonatoms in the alkyl part, the radicals in each case being optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, and phenylalkenyl which has 2 to 4 carbon atomsin the alkenyl part and is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, particularlypreferred phenyl substituents being:

fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, methylthio,ethyl, ethoxy, ethylthio, n- and i-propyl, isopropoxy, n-, iso-, sec.-and t-butyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,cyclohexyl, methoxycarbonyl, ethoxycarbonyl and phenoxy or phenyl whichis optionally substituted by fluorine, chlorine or methyl;

R² represents straight-chain or branched alkyl having 1 to 10 carbonatoms, benzyl and phenyl which is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituents,suitable phenyl or benzyl substituents in each case being: fluorine,chlorine, bromine, cyano, nitro, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, methoxycarbonyl and ethoxycarbonyl, or representscyclopropyl, cyclopentyl and cyclohexyl,

R³ represents methyl, ethyl, n- and i-propyl, n-, i-, sec.- and t-butyl,n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-dodecyl,allyl, propargyl, 2-butenyl, cyclopentyl or cyclohexyl, and phenyl orbenzyl, each of which is optionally monosubstituted or disubstituted byidentical or different substituents from the group comprising fluorine,chlorine, methyl and trifluoromethyl, and

R⁴ represents n- and i-propyl, n-, i-, sec.- and t-butyl, n-pentyl,n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, allyl, propargyl,but-2-enyl, cyclopentyl or cyclohexyl, and phenyl or benzyl, each ofwhich is optionally monosubstituted or disubstituted by identical ordifferent substituents from the group comprising fluorine, chlorine,methyl and trifluoromethyl; or

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl,morpholin-4-yl, perhydroazepin-1-yl, imidazol-1-yl, 1,2,4-triazol-1-ylor pyrazol-1-yl, each of which is optionally monosubstituted,disubstituted or trisubstituted by identical or different substituents,particularly preferred substituents being: methyl, ethyl, n- andi-propyl, phenyl, methoxycarbonyl and ethoxycarbonyl.

Very particularly preferred substituted aminoketals of the formula (I)are those in which

R¹ represents straight-chain or branched alkyl having 1 to 5 carbonatoms, and phenylalkenyl, phenylalkyl, phenoxyalkyl, benzyloxyalkyl,phenylthioalkyl, phenylsulphinylalkyl and phenylsulphonylalkyl, each ofwhich has up to 5 carbon atoms in the alkyl part or alkenyl part and isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents, the following being mentioned as phenylsubstituents:

fluorine, chlorine, bromine, methyl, ethyl, n- and i-propyl, t-butyl-,methoxy, ethoxy, isopropoxy, cyclohexyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,nitro, cyano, phenyl and phenoxy;

R² represents straight-chain or branched alkyl having 1 to 4 carbonatoms or hydrogen;

R³ represents methyl, ethyl, n- and i-propyl or n-, i- and t-butyl;

R⁴ represents methyl, ethyl, n- and i-propyl, n- and i-butyl, pentyl orhexyl, or

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent piperidin-1-yl, perhydroazepin-1-yl, pyrrolidin-1-yl,morpholin-4-yl, piperazin-1-yl, imidazol-1-yl and 1,2,4-triazol-1-yl,each of which is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, the followingbeing mentioned as substituents: alkyl having 1 to 3 carbon atoms,methoxycarbonyl, ethoxycarbonyl and phenyl.

Substituted aminoketals of the formula (I) which may be mentioned inparticular are those in which

R¹ represents the groupings ##STR3## R⁵ represents phenyl, phenoxy,phenylthio, phenylsulphinyl or phenylsulphonyl, each of which isoptionally monosubstituted to trisubstituted by identical or differentsubstituents, the following being mentioned as substituents: fluorine,chlorine, bromine, nitro, cyclohexyl, straight-chain or branched alkylhaving 1 to 4 carbon atoms, straight-chain or branched alkoxy having 1to 3 carbon atoms and alkoxycarbonyl having 1 or 2 carbon atoms in thealkoxy part,

R² represents a straight-chain or branched alkyl having 1 to 4 carbonatoms,

R³ represents a straight-chain or branched alkyl having 1 to 4 carbonatoms or straight-chain or branched alkenyl having 3 to 5 carbon atoms,

R⁴ represents straight-chain or branched alkyl having 1 to 4 carbonatoms, and

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent a piperidine, morpholine or pyrrolidine radical which isoptionally monosubstituted to trisubstituted by identical or differentalkyl radicals having 1 to 3 carbon atoms,

as well as those aminoketals of the formula (I) in which

R¹ represents the groupings ##STR4## wherein R⁶ represents phenyl whichis in each case optionally monosubstituted to trisubstituted byidentical or different substituents, the following being mentioned assubstituents: fluorine, chlorine, bromine, nitro, cyclohexyl,straight-chain or branched alkyl or alkoxy, each having 1 to 4 carbonatoms, an alkoxycarbonyl having 1 or 2 carbon atoms in the alkoxy part,

R² represents straight-chain or branched alkyl having 1 to 4 carbonatoms,

R³ represents straight-chain or branched alkyl having 1 to 4 carbonatoms or straight-chain or branched alkenyl having 3 to 5 carbon atoms,

R⁴ represents straight-chain or branched alkyl having 1 to 4 carbonatoms, and

R³ and R⁴, together with the nitrogen atom to which they are bonded,represent a piperidine, morpholine or pyrrolidine radical which isoptionally monosubstituted to trisubstituted by identical or differentalkyl radicals having 1 to 3 carbon atoms.

The addition products of acids and the substituted aminoketals of theformula (I) and metal salt complexes of compounds of the formula (I) arealso compounds which can be used according to the invention.

To prepare physiologically tolerated acid addition salts of thecompounds of the formula (I), the following acids are preferred:hydrohalic acids, such as, for example, hydrochloric acid andhydrobromic acid, in particular hydrochloric acid, and also phosphoricacid, nitric acid, sulphuric acid, monofunctional and bifunctionalcarboxylic acids and hydroxycarboxylic acids, such as, for example,acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid,citric acid, salicylic acid, sorbic acid and lactic acid, as well assulphonic acids, such as, for example, p-toluenesulphonic acid andnaphthalene-1,5-disulphonic acid.

The acid addition salts of the compounds of the formula (I) can beobtained in a simple manner by customary salt formation methods, forexample by dissolving a compound of the formula (I) in a suitableorganic solvent and adding the acid, for example hydrochloric acid, andcan be isolated in a known manner, for example by filtration, and ifappropriate purified by washing with an inert organic solvent.

Preferred salts for the preparation of metal salt complexes of thecompounds of the formula (I) are those of metals of main groups II to IVand of subgroups I and II and IV to VIII, and copper, zinc, manganese,magnesium, tin, iron and nickel may be mentioned as examples.

Some of the substituted aminoketals of the formula (I) which are to beused according to the invention are known. The known compounds, as wellas the new substituted aminoketals of the formula (IA) ##STR5## in whichR^(1'), R^(2'), R^(3') and R^(4') have the meaning given further below,can be prepared by processes which are known from the literature, byreacting substituted dioxolanes of the general formula (II) ##STR6## inwhich R^(1') and R^(2') have the meaning given further below and Xrepresents halogen, optionally substituted alkylsulphonyloxy orarylsulphonyloxy,

with amines of the general formula (III) ##STR7## in which R^(3') andR^(4') have the meaning given further below, if appropriate in thepresence of a catalyst and, if appropriate, in the presence of a baseand, if appropriate in the presence of a diluent.

In the formula (IA), the substituents have the following meaning:

R^(1') represents a straight-chain or branched alkyl having 6 to 18carbon atoms; substituted alkyl, such as straight-chain or branchedhalogenoalkyl having 2 to 12 carbon atoms and 1 to 5 halogen atoms,straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in thealkyl part, benzyl which is monosubstituted or polysubstituted byidentical or different substituents, arylalkyl which has 2 to 6 carbonatoms in the alkyl part and 6 to 10 carbon atoms in the aryl part and isoptionally monosubstituted or polysubstituted by identical or differentsubstituents, and aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphinylalkyl and arylsulphonylalkyl, each of which has 1 to 6carbon atoms in each alkyl part and 6 to 10 carbon atoms in the arylpart, suitable aryl or benzyl substituents in each case being:

halogen, cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 to 4carbon atoms; halogenoalkyl, halogenoalkoxy and halogenoalkylthio, eachhaving 1 or 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5to 7 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in thealkyl part, and phenoxy or phenyl which is optionally substituted byhalogen, in particular fluorine or chlorine, or by alkyl having 1 to 4carbon atoms; cycloalkylalkyl having 1 to 4 carbon atoms and 3 to 7atoms in the cycloalkyl part which is optionally monosubstituted orpolysubstituted by alkyl having 1 to 4 carbon atoms; and also representsstraight-chain or branched alkenyl having 2 to 5 carbon atoms,straight-chain or branched alkinyl having 2 to 6 carbon atoms;cycloalkyl which has 3 to 7 carbon atoms and is monosubstituted orpolysubstituted by identical or different alkyl radicals having 1 to 4carbon atoms, and represents arylalkenyl having 2 to 6 carbon atoms inthe alkenyl part and 6 to 10 atoms in the aryl part, suitable arylsubstituents in each case being:

halogen, cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 or 2carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part,phenyl or phenoxy which is optionally substituted by halogen, inparticular fluorine or chlorine, or by alkyl having 1 to 4 carbon atoms;

R^(2') represents hydrogen, straight-chain or branched alkyl having 1 to18 carbon atoms; substituted alkyl, such as straight-chain or branchedhalogenoalkyl having 1 to 12 carbon atoms and 1 to 5 halogen atoms,straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in thealkyl part, arylalkyl, aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphinylalkyl and arylsulphonylalkyl, each of which has 1 to 6carbon atoms in each alkyl part and 6 to 10 carbon atoms in the arylpart and is optionally monosubstituted or polysubstituted by identicalor different substituents, suitable aryl substituents in each casebeing:

halogen, cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 to 4carbon atoms; halogenoalkyl, halogenoalkoxy and halogenoalkylthio, eachhaving 1 or 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5to 7 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in thealkyl part, and phenoxy or phenyl which is optionally substituted byhalogen, in particular fluorine or chlorine, or by alkyl having 1 to 4carbon atoms; and cycloalkyl having 1 to 4 carbon atoms in the alkylpart and 3 to 7 carbon atoms in the cycloalkyl part which is optionallymonosubstituted or polysubstituted by alkyl having 1 to 4 carbon atoms,and also represents straight-chain or branched alkenyl or alkinyl, eachhaving 2 to 6 carbon atoms, cycloalkyl which has 3 to 7 carbon atoms andis optionally monosubstituted or polysubstituted by identical ordifferent alkyl radicals having 1 to 4 carbon atoms, or represents arylhaving 6 to 10 carbon atoms and arylalkenyl having 2 to 6 carbon atomsin the alkenyl part and 6 to 10 carbon atoms in the aryl part, each ofwhich is optionally monosubstituted or polysubstituted by identical ordifferent substituents, suitable aryl substituents being: halogen,cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 to 4 carbonatoms; halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having1 to 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkylpart, and phenoxy or phenyl which is optionally substituted by halogen,in particular fluorine or chlorine, or by alkyl having 1 to 4 carbonatoms;

R^(3') represents straight-chain or branched alkyl having 1 to 12 carbonatoms, straight-chain or branched alkenyl having 3 to 12 carbon atoms,straight-chain or branched alkinyl having 3 to 7 carbon atoms,cycloalkyl which has 5 to 7 carbon atoms and is optionallymonosubstituted or polysubstituted by identical or different alkylradicals having 1 to 4 carbon atoms, and represents aryl having 6 to 10carbon atoms and aralkyl having 1 or 2 carbon atoms in the alkyl partand 6 to 10 carbon atoms in the aryl part, each of which is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, suitable aryl substituents in each case being:

halogen, alkyl having 1 to 4 carbon atoms and halogenoalkyl having 1 or2 carbon atoms and 1 to 5 halogen atoms;

R^(4') represents straight-chain or branched alkyl having 1 to 12 carbonatoms, straight-chain or branched alkenyl having 3 to 12 carbon atoms,straight-chain or branched alkinyl having 3 to 7 carbon atoms,cycloalkyl which has 5 to 7 carbon atoms and is optionallymonosubstituted or polysubstituted by identical or different alkylradicals having 1 to 4 carbon atoms, and aryl having 6 to 10 carbonatoms or aralkyl having 1 to 2 carbon atoms in the alkyl part and 6 to10 carbon atoms in the aryl part, each of which is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, suitable aryl substituents in each case being:

halogen, alkyl having 1 to 4 carbon atoms, and halogenoalkyl having 1 to2 carbon atoms and 1 to 5 halogen atoms; or

R^(3') and R^(4'), together with the nitrogen atom to which they arebonded, represent a 5-membered to 7-membered, saturated or unsaturatedhetercyclic structure which has 1 to 3 hetero atoms, preferably nitrogenor oxygen, and is optionally monosubstituted or polysubstituted byidentical or different substituents, the following being preferablymentioned as substituents: alkyl having 1 to 4 carbon atoms,alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, and phenyl.

Particularly preferred substituted aminoketals of the formula (IA) arethose in which

R^(1') represents straight-chain or branched alkyl having 6 to 12 carbonatoms; straight-chain or branched halogenoalkyl having 2 to 6 carbonatoms and 1 to 5 halogen atoms, cyanomethyl or cyanoethyl, benzyl whichis monosubstituted to trisubstituted by identical or differentsubstituents, phenylalkyl which has 2 to 6 carbon atoms in the alkylpart and is optionally monosubstituted to trisubstituted by identical ordifferent substituents, and phenoxyalkyl, phenylalkoxyalkyl,phenylthioalkyl, phenylsulphinylalkyl and phenylsulphonylalkyl, each ofwhich has 1 to 4 carbon atoms in each alkyl part, suitable phenyl orbenzyl substituents in each case being:

fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, methylthio,ethyl, ethoxy, ethylthio, n- and i-propyl, isopropoxy, n-, iso-, sec.-and t-butyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,cyclohexyl, methoxycarbonyl and ethoxycarbonyl, and phenoxy or phenylwhich is optionally substituted by fluorine, chlorine or methyl; andalso represents cycloalkylalkyl having 1 to 4 carbon atoms in the alkylpart and 5 to 7 carbon atoms in the cycloalkyl part which is optionallymonosubstituted or polysubstituted by alkyl having 1 to 4 carbon atoms;and also represents straight-chain or branched alkenyl having 3 to 5carbon atoms, straight-chain or branched alkinyl having 3 to 6 carbonatoms; cycloalkyl which has 5 to 7 carbon atoms and is monosubstitutedto trisubstituted by identical or different substituents from amongstmethyl, ethyl or propyl, and represents phenylalkenyl having 2 to 5carbon atoms in the alkenyl part, suitable phenyl substituents in eachcase being: fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy,methylthio, ethyl, ethoxy, ethylthio, n- and i-propyl, isopropoxy, n-,iso-, sec.- and t-butyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, cyclohexyl, methoxycarbonyl and ethoxycarbonyl, andphenoxy or phenyl which is optionally substituted by fluorine, chlorineor methyl;

R^(2') represents hydrogen, straight-chain or branched alkyl having 1 to10 carbon atoms; and benzyl or phenyl which is optionallymonosubstituted to trisubstituted by identical or differentsubstituents, suitable phenyl or benzyl substituents in each case being:

fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, methoxycarbonyl andethoxycarbonyl,

R^(3') represents methyl, ethyl, n- and i-propyl, n-, i-, sec.- andt-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl,n-dodecyl, allyl, propargyl, but-2-enyl, cyclopentyl and cyclohexyl, andbenzyl or phenyl, each of which is optionally monosubstituted ordisubstituted by identical or different substituents from amongstfluorine, chlorine, methyl or trifluoromethyl, and

R^(4') represents n- and i-propyl, n-, i-, sec.- and t-butyl, n-pentyl,n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, allyl, propargyl,but-2-enyl, cyclopentyl and cyclohexyl, and phenyl or benzyl, each ofwhich is optionally monosubstituted or disubstituted by identical ordifferent substituents from amongst fluorine, chlorine, methyl andtrifluoromethyl; or

R^(3') and R^(4'), together with the nitrogen atom to which they arebonded, represent pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl,morpholin-4-yl, perhydroazepin-1-yl, imidazol-1-yl, 1,2,4-triazol-1-ylor pyrazol-1-yl, each of which is optionally monosubstituted totrisubstituted by identical or different substituents, particularlypreferred substituents being:

methyl, ethyl, n- and i-propyl, phenyl, methoxycarbonyl andethoxycarbonyl.

Substituted aminoketals of the formula (IA) which may be mentioned inparticular are those in which

R^(1') represents the groupings ##STR8## wherein R⁵ represents phenyl,phenoxy, phenylthio, phenylsulphinyl or phenylsulphonyl, each of whichis optionally monosubstituted to trisubstituted by identical ordifferent substituents, the following being mentioned as substituents:fluorine, chlorine, bromine, nitro, cyclohexyl, straight-chain orbranched alkyl having 1 to 4 carbon atoms, straight-chain or branchedalkoxy having 1 to 3 carbon atoms and alkoxycarbonyl having 1 or 2carbon atoms in the alkoxy part,

R^(2') represents straight-chain or branched alkyl having 1 to 4 carbonatoms,

R^(3') represents straight-chain or branched alkyl having 1 to 4 carbonatoms or straight-chain or branched alkenyl having 3 to 5 carbon atoms,

R^(4') represents straight-chain or branched alkyl having 1 to 4 carbonatoms, and

R^(3') and R^(4'), together with the nitrogen atom to which they arebonded, represent a piperidine, morpholine or pyrrolidine radical whichis optionally monosubstituted to trisubstituted by identical ordifferent alkyl radicals having 1 to 3 carbon atoms,

as well as those aminoketals of the formula (IA), in which

R^(1') represents the groupings ##STR9## wherein R⁶ represents phenylwhich in each case is optionally monosubstituted to trisubstituted byidentical or different substituents, the following being mentioned assubstituents: fluorine, chlorine, bromine, nitro, cyclohexyl,straight-chain or branched alkyl or alkoxy, each having 1 to 4 carbonatoms, and alkoxycarbonyl having 1 or 2 carbon atoms in the alkoxy part,

R^(2') represents straight-chain or branched alkyl having 1 to 4 carbonatoms,

R^(3') represents straight-chain or branched alkyl having 1 to 4 carbonatoms or straight-chain or branched alkenyl having 3 to 5 carbon atoms,

R^(4') represents straight-chain or branched alkyl having 1 to 4 carbonatoms, and

R^(3') and R^(4'), together with the nitrogen atom to which they arebonded, represent the piperidine, morpholine or pyrrolidine radicalwhich is optionally monosubstituted to trisubstituted by identical ordifferent alkyl radicals having 1 to 3 carbon atoms.

Formula (II) gives a general definition of the substituted dioxolanesrequired as starting materials in carrying out the stated process. Inthis formula, R^(1') and R^(2') preferably have those meanings whichhave already been mentioned in connection with the description of thesubstances according to the invention, of the formula (IA), as beingpreferred for these radicals. X preferably represents chlorine, bromine,methanesulphonyloxy, p-toluenesulphonyloxy ortrifluoromethanesulphonyloxy.

Some of the substituted dioxolanes of the formula (II) are known [see,for example: Rec. Trav. Chim. Pays-Bas 91, 989-1001 (1972) Farm. Ed.Sci. 29, 167-174, (1974), and J. med. Chem. 6 (1963), 3, 325-328], orcan be obtained by processes similar to those described in thesereferences, by reacting, for example, aldehydes or ketones of theformula ##STR10## in which R^(1') and R^(2') have the meaning givenabove, in a customary manner with substituted 1,2-diols of the formula##STR11## in which X has the meaning given above, in the presence of aninert organic solvent, such as, for example, toluene, and in thepresence of a catalyst, such as, for example, p-toluenesulphonic acid,at temperatures between 50° C. and 120° C.

Formula (III) gives a general definition of the amines additionallyrequired as starting materials for the stated process. In this formula,R^(3') and R^(4') preferably represent those radicals which have alreadybeen mentioned in connection with the description of the substancesaccording to the invention, of the formula (IA), as being preferred forthese substituents.

The amines of the formula (III) are generally known compounds of organicchemistry.

Organic solvents are suitable diluents for the process. Such solventspreferably include aromatic hydrocarbons, such as benzene, toluene orxylene; halogenated hydrocarbons, such as carbon tetrachloride orchlorobenzene; formamides such as dimethylformamide; nitriles, such asacetonitrile or propionitrile; alcohols, such as propanol or butanol;amines, such as triethylamine or piperidine; and the highly polarsolvents dimethylsulphoxide or hexamethylphosphoric acid triamide.

The process is carried out, if appropriate, in the presence of a base asan acid-binding agent. All customary organic and, in particular,inorganic bases can be employed for this purpose. These preferablyinclude alkali metal hydroxides or carbonates, such as, for example,sodium hydroxide, sodium carbonate or potassium carbonate; and alsotriethylamine and pyridine. If desired, the amines of the formula (III)which are employed as starting materials may also be used as solventsand as acid-binding agents.

The process is carried out, if appropriate, in the presence of acatalyst. Alkali metal iodides, such as, for example, potassium iodide,are preferably used.

In the process, the reaction temperatures can be varied within arelatively wide range. In general, the reaction is carried out atbetween 50° C. and 250° C., preferably between 80° C. and 200° C.

The process can be carried out under atmospheric pressure or underelevated pressure. In general, the reaction is carried out at pressuresbetween about 1.5 atm and 5 atm, preferably between 1.5 atm and 3 atm.

In carrying out the process, 1 to 30 mols of the amine of the formula(III), depending on whether the amine is also used as a diluent and/oran acid-binding agent, are preferably employed per mol of substituteddioxolane of the formula (II). The isolation of the end products iseffected by customary methods.

Suitable anions of the salts are those which are preferably derived fromthe following acids: hydrohalic acids, such as, for example,hydrochloric acid and hydrobromic acid, and also phosphoric acid, nitricacid and sulphuric acid.

The metal salt complexes of compounds of the formula (I) or (IA) can beobtained in a simple manner by customary processes, thus, for example,by dissolving the metal salt in an alcohol, for example ethanol, andadding the solution to the compound of the formula (I) or (IA). Metalsalt complexes can be purified in a known manner, for example byfiltration, isolating and if appropriate by recrystallization.

The active compounds according to the invention exhibit a powerfulmicrobicidal action and can be employed in practice for combatingundesired micro-organisms. The active compounds are suitable for use asplant protection agents.

Fungicidal agents in plant protection are employed for combatingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericidal agents are employed in plant protection for combatingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

The good toleration, by plants, of the active compounds, at theconcentrations required for combating plant diseases, permits treatmentof above-ground parts of plants, of vegetative propagation stock andseeds, and of the soil.

As plant protection agents, the active compounds according to theinvention can be used with particularly good success for combatingcereal diseases, such as, for example, against the powdery mildew ofbarley causative organism (Erysiphe graminis) or the stripe diseasecausative organism (Drechslera graminea), rice diseases, such as, forexample, Pyricularia oryzae, or potato diseases, such as, for example,against the potato blight causative organism (Phytophtora infestans).

The active compounds can be converted to the customary formulations,such as solutions, emulsions, suspensions, powders, foams, pastes,granules aerosols, very fine capsules in polymeric substances and incoating compositions for seed and ULV formulations.

These formulations are produced in known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. In the case of the use of water asan extender, organic solvents can, for example, also be used asauxiliary solvents. As liquid solvents, there are suitable in the main:aromatics, such as xylene, toluene or alkyl naphthalenes, chlorinatedaromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethylsulphoxide, as well as water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at normal temperature andunder normal pressure, for example aerosol propellants, such ashalogenated hydrocarbons as well as butane, propane, nitrogen and carbondioxide; as solid carriers there are suitable: for example groundnatural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly-dispersed silicic acid, alumina and silicates;as solid carriers for granules there are suitable: for example crushedand fractionated natural rocks such as calcite, marble, pumice,sepiolite and dolomite, as well as synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, corn cobs and tobacco stalks; as emulsifying and/or foam-formingagents there are suitable: for example non-ionic and anionicemulsifiers, such as polyoxyethylene-fatty acid esters,polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycolethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well asalbumin hydrolysis products; as dispersing agents there are suitable:for example ligninsulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, can be used in theformulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be present in theformulations as a mixture with other known compounds, such asfungicides, insecticides, acaricides, herbicides, bactericides,nematicides, bird repellents, growth factors, plant nutrients and agentsfor improving soil structure.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusting agents and granules.They are used in the customary manner, for example by watering,spraying, atomizing, scattering, dusting, foaming, brushing, etc. It isalso possible to apply the active compounds by the ultra-low-volumemethod, or to inject the formulation of active compound, or the activecompound itself, into the soil. It is also possible to treat the seed ofthe plants.

In the treatment of parts of plants, the active compound concentrationsin the use forms can be varied within a substantial range. They are, ingeneral, between 1 and 0.0001% by weight, preferably between 0.5 and0.001%.

In the treatment of seed, amounts of active compound of 0.001 to 50 gper kilogram of seed, preferably 0.01 to 10 g are generally required.

For the treatment of soil, active compound concentrations of 0.00001 to0.1% by weight, preferably 0.0001 to 0.02%, are required at the place ofaction.

PREPARATION EXAMPLES EXAMPLE 1 ##STR12##

17.3 g (0.05 mol) of2-(t-butyl)-2-(4-chlorophenoxymethyl)-4-methanesuylphonyloxymethyl-1,3-dioxolaneand 7.1 g (0.1 mol) of pyrrolidine are heated at 120° C. for 15 hours.After the mixture has been cooled, excess pyrrolidine is distilled offin vacuo, and the residue is taken up in ether. The ether solution iswashed twice with water, dried over sodium sulphate and evaporated downin vacuo.

12.1 g (65.7% of theory) of2-(t-butyl)-2-(4-chlorophenoxymethyl)-4-(pyrrolidin-1-ylmethyl)-1,3-dioxolaneare obtained as an oil of refractive index n_(D) ²⁰ 1.5099.

Preparation of the starting material: ##STR13##

142 g (0.5 mol) of2-(t-butyl)-2-(4-chlorophenoxymethyl)-4-hydroxymethyl-1,3-dioxolane aretaken up in 150 ml of pyridine and 57 g (0.5 mol) of methanesulphonylchloride are added dropwise at 0° C. The mixture is stirred for 17 hoursat 20° C.-25° C., and the solvent is then distilled off in vacuo. Theresidue is taken up in ether, and the ether solution is washed withwater, dried over sodium sulphate and evaporated down in vacuo.

171 g (98% of theory) of2-(t-butyl)-2-(4-chlorophenoxymethyl)-4-methanesulphonyloxymethyl-1,3-dioxolaneare obtained as an oil.

¹ H-NMR (CDCl₃): δ(ppm)=7.2 (d, 2H), 6.8 (d, 2H), 4.6-3.6 (m, 7H), 3.0(d, 3H), 1.05 (s, 9H). ##STR14##

226 g (1 mol) of 1-(4-chlorophenoxy)-3,3-dimethylbutan-2-one (obtainedfrom sodium 4-chlorophenolate and α-bromopinacolone; in this respect,see German Patent Specification No. 2,201,063), together with 120 g(1.07 mols) of glycerol, 19 g (0.1 mol) of p-toluenesulphonic acidmonohydrate and 30 ml of butanol, are dissolved in 1,000 ml of toluene,and the mixture is heated under reflux for 16 hours in a waterseparator. After the mixture has been cooled, the toluene phase iswashed with 4 times 250 ml of water, dried over magnesium sulphate,filtered, and evaporated down in vacuo. 186 g (65.4% of theory) of2-(t-butyl)-2-(4-chlorophenoxymethyl)-4-hydroxymethyl-1,3-dioxolane ofboiling point b.p. ₀.1 : 161° C.-163° C. are obtained by distillation.

EXAMPLE 2 ##STR15##

16.1 g (0.05 mol) of4-chloromethyl-2-(4-chlorophenylmethyl)-2-phenyl-1,3-dioxolane, 100 mlof di-n-butylamine and 13.8 g (0.1 mol) of potassium carbonate togetherwith a pinch of potassium iodide are stirred for 8 hours at 180° C. and2 bar in an autoclave.

To work up the mixture, the excess di-n-butylamine is removed undervacuum from a water jet, at a bath temperature of 40° C.-100° C. Theresidue, when it is cold, is taken up in 50 ml of toluene, and thesolution is filtered and evaporated down in vacuo.

9.4 g (47% of theory) of2-(4-chlorophenylmethyl)-4-(N,N-di-n-butylaminomethyl)-2-phenyl-1,3-dioxolaneare obtained as an oil of refractive index n_(D) ²⁰ =1.5172.

Preparation of the starting material: ##STR16##

69 g (0.3 mol) of phenyl 4-chlorophenylmethyl ketone, 66.3 (0.6 mol) of3-chloropropane-1,2-diol and 5.2 g (0.03 mol) of p-toluenesulphonic acidin 600 ml of toluene are refluxed for three days in a water separator.The reaction mixture, when it is cold, is extracted with sodiumbicarbonate solution, dried over sodium sulphate and evaporated down invacuo.

95 g (98% of theory) of4-chloromethyl-2-(4-chlorophenylmethyl)-2-phenyl-1,3-dioxolane ofmelting point 65° C. are obtained.

EXAMPLE 3 ##STR17##

16.1 g (0.05 mol) of4-chloromethyl-2-(4-chlorophenylmethyl)-2-phenyl-1,3-dioxolane (for thepreparation see Example 2), 100 g (1.18 mols) of piperidine, 1.38 g (0.1mol) of potassium carbonate and a pinch of potassium iodide are boiledunder reflux together for 16 hours. The reaction mixture is evaporateddown in vacuo, the residue is taken up in 150 ml of 0.4N hydrochloricacid, and the solution is washed 3 times with 50 ml of ligroin. Thesolution containing hydrochloric acid is saturated with sodium chlorideand extracted 3 times with 60 ml of ethyl acetate. The ethyl acetatephase is washed with sodium bicarbonate solution and sodium chloridesolution, dried over sodium sulphate, and freed from solvent in vacuo ata bath temperature of 40° C.

10 g (53.8% of theory) of2-(4-chlorophenylmethyl)-2-phenyl-4-(piperidin-1-ylmethyl)-1,3-dioxolaneare obtained as a wax-like solid residue of melting point 58° C.

The following compounds of the formula (I) ##STR18## were obtained in acorresponding manner and according to the stated process:

    __________________________________________________________________________     No.Example                                                                         R.sup.1              R.sup.2                                                                                 ##STR19##      refractive index                                                             (n.sub.D.sup.20)Melting                                                        point (°C.)        __________________________________________________________________________                                                       or                         4    C.sub.2 H.sub.5      CH.sub.3                                                                                 ##STR20##     1.5027                       5  C.sub.2 H.sub.5      CH.sub.3                                                                                 ##STR21##     1.5036                       6  C.sub.2 H.sub.5      CH.sub.3                                                                                 ##STR22##     1.5012                       7  C.sub.2 H.sub.5      CH.sub.3                                                                                 ##STR23##     1.5047                       8  C.sub.2 H.sub.5      CH.sub.3                                                                                 ##STR24##     1.4682                       9  i-C.sub.4 H.sub.9    CH.sub.3                                                                                 ##STR25##     1.5039                       10 i-C.sub.4 H.sub.9    CH.sub.3                                                                                 ##STR26##     1.5041                       11 i-C.sub.4 H.sub. 9   CH.sub.3                                                                                 ##STR27##     1.5035                       12 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR28##     1.4570                       13 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR29##     1.4535                       14 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR30##     1.4549                       15 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR31##     1.4489                       16 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR32##     1.4510                       17 n-C.sub.9 H.sub.19   CH.sub.3                                                                                 ##STR33##     1.4551                       18 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR34##     1.4510                       19 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR35##     1.4588                       20 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR36##     1.4578                       21 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR37##     1.4539                       22 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR38##     1.4534                       23 n-C.sub.9 H.sub.19   n-C.sub.9 H.sub.19                                                                       ##STR39##     1.4555                       24                                                                                ##STR40##           CH.sub.3                                                                                 ##STR41##     1.5301                       25                                                                                ##STR42##           CH.sub.3                                                                                 ##STR43##     1.5326                       26                                                                                ##STR44##           CH.sub.3                                                                                 ##STR45##     1.5084                       27                                                                                ##STR46##           CH.sub.3                                                                                 ##STR47##     1.5372                       28                                                                                ##STR48##           CH.sub.3                                                                                 ##STR49##     1.5219                       29                                                                                ##STR50##           CH.sub.3                                                                                 ##STR51##     1.5383                       30                                                                                ##STR52##           CH.sub.3                                                                                 ##STR53##     1.5384                       31                                                                                ##STR54##           CH.sub.3                                                                                 ##STR55##     1.5181                       32                                                                                ##STR56##           C.sub.6 H.sub.5                                                                          ##STR57##     61                           33                                                                                ##STR58##           C.sub.6 H.sub.5                                                                          ##STR59##     71                           34                                                                                ##STR60##           CH.sub.3                                                                                 ##STR61##     1.5261                       35                                                                                ##STR62##           CH.sub.3                                                                                 ##STR63##     1.5244                       36                                                                                ##STR64##           CH.sub.3                                                                                 ##STR65##     1.5282                       37                                                                                ##STR66##           t-C.sub.4 H.sub.9                                                                        ##STR67##     1.4889                       38                                                                                ##STR68##           t-C.sub.4 H.sub.9                                                                        ##STR69##     1.5003                       39                                                                                ##STR70##           t-C.sub.4 H.sub.9                                                                        ##STR71##     98                           40                                                                                ##STR72##           t-C.sub.4 H.sub.9                                                                        ##STR73##     121                          41                                                                                ##STR74##           t-C.sub.4 H.sub.9                                                                        ##STR75##     1.5049                       42                                                                                ##STR76##           t-C.sub.4 H.sub.9                                                                        ##STR77##     1.5173                       43                                                                                ##STR78##           t-C.sub.4 H.sub.9                                                                        ##STR79##     1.5068                       44                                                                                ##STR80##           t-C.sub.4 H.sub.9                                                                        ##STR81##     1.5026                       45                                                                                ##STR82##           t-C.sub.4 H.sub.9                                                                        ##STR83##     1.5032                       46                                                                                ##STR84##           t-C.sub.4 H.sub.9                                                                        ##STR85##     1.5012                       47                                                                                ##STR86##           t-C.sub.4 H.sub.9                                                                        ##STR87##     40                           48                                                                                ##STR88##           t-C.sub.4 H.sub.9                                                                        ##STR89##     1.5082                       49                                                                                ##STR90##           t-C.sub.4 H.sub.9                                                                        ##STR91##     1.5187                       50                                                                                ##STR92##           t-C.sub.4 H.sub.9                                                                        ##STR93##     1.5271                       51                                                                                ##STR94##           t-C.sub.4 H.sub.9                                                                        ##STR95##     1.5126                       52                                                                                ##STR96##           t-C.sub.4 H.sub.9                                                                        ##STR97##     1.4917                       53                                                                                ##STR98##           t-C.sub.4 H.sub.9                                                                        ##STR99##     1.5026                       54                                                                                ##STR100##          t-C.sub.4 H.sub.9                                                                        ##STR101##    1.4992                       55                                                                                ##STR102##          t-C.sub.4 H.sub.9                                                                        ##STR103##    1.5023                       56                                                                                ##STR104##          t-C.sub.4 H.sub.9                                                                        ##STR105##    1.5045                       57                                                                                ##STR106##          t-C.sub.4 H.sub.9                                                                        ##STR107##    1.5008                       58                                                                                ##STR108##          t-C.sub.4 H.sub.9                                                                        ##STR109##    1.4938                       59                                                                                ##STR110##          t-C.sub.4 H.sub.9                                                                        ##STR111##    134                          60                                                                                ##STR112##          t-C.sub.4 H.sub.9                                                                        ##STR113##    1.5109                       61                                                                                ##STR114##          t-C.sub.4 H.sub.9                                                                        ##STR115##    1.5226                       62                                                                                ##STR116##          t-C.sub.4 H.sub.9                                                                        ##STR117##    1.5577                       63                                                                                ##STR118##          t-C.sub.4 H.sub.9                                                                        ##STR119##    1.5557                       64                                                                                ##STR120##          CH.sub.3                                                                                 ##STR121##    1.5011                       65                                                                                ##STR122##          CH.sub.3                                                                                 ##STR123##    1.4998                       66                                                                                ##STR124##          CH.sub.3                                                                                 ##STR125##    1.4973                       67                                                                                ##STR126##          CH.sub.3                                                                                 ##STR127##    1.4939                       68                                                                                ##STR128##          CH.sub.3                                                                                 ##STR129##    1.4974                       69                                                                                ##STR130##          CH.sub.3                                                                                 ##STR131##    1.5200                       70                                                                                ##STR132##          CH.sub.3                                                                                 ##STR133##    1.5121                       71                                                                                ##STR134##          CH.sub.3                                                                                 ##STR135##    153-155                      72                                                                                ##STR136##          CH.sub.3                                                                                 ##STR137##    1.5102                       73                                                                                ##STR138##          CH.sub.3                                                                                 ##STR139##    1.5431                       74                                                                                ##STR140##          CH.sub.3                                                                                 ##STR141##    1.5191                       75                                                                                ##STR142##          CH.sub.3                                                                                 ##STR143##    1.4993                       76                                                                                ##STR144##          CH.sub.3                                                                                 ##STR145##    1.5377                       77                                                                                ##STR146##          CH.sub.3                                                                                 ##STR147##    1.5150                       78                                                                                ##STR148##          CH.sub.3                                                                                 ##STR149##    100 (× HCl)            79                                                                                ##STR150##          CH.sub.3                                                                                 ##STR151##    1.5047                       80                                                                                ##STR152##          CH.sub.3                                                                                 ##STR153##    1.5051                       81                                                                                ##STR154##          CH.sub.3                                                                                 ##STR155##    1.5006                       82                                                                                ##STR156##          CH.sub.3                                                                                 ##STR157##    1.4941                       83                                                                                ##STR158##          CH.sub.3                                                                                 ##STR159##    1.5034                       84                                                                                ##STR160##          CH.sub.3                                                                                 ##STR161##    1.4987                       85                                                                                ##STR162##          CH.sub.3                                                                                 ##STR163##    1.4980                       86                                                                                ##STR164##          CH.sub.3                                                                                 ##STR165##    1.5021                       87                                                                                ##STR166##          CH.sub.3                                                                                 ##STR167##    1.4980                       88                                                                                ##STR168##          CH.sub.3                                                                                 ##STR169##    1.5034                       89                                                                                ##STR170##          CH.sub.3                                                                                 ##STR171##    1.4952                       90                                                                                ##STR172##          CH.sub.3                                                                                 ##STR173##    1.4874                       91                                                                                ##STR174##          CH.sub.3                                                                                 ##STR175##    1.5023                       92                                                                                ##STR176##          CH.sub.3                                                                                 ##STR177##    1.5132                       93                                                                                ##STR178##          CH.sub.3                                                                                 ##STR179##    1.5118                       94                                                                                ##STR180##          CH.sub.3                                                                                 ##STR181##    1.5081                       95                                                                                ##STR182##          CH.sub.3                                                                                 ##STR183##    1.5064                       96                                                                                ##STR184##          CH.sub.3                                                                                 ##STR185##    1.5086                       97                                                                                ##STR186##          CH.sub.3                                                                                 ##STR187##    1.5087                       98                                                                                ##STR188##          CH.sub.3                                                                                 ##STR189##    1.5074                       99                                                                                ##STR190##          CH.sub.3                                                                                 ##STR191##    1.5067                       100                                                                               ##STR192##          CH.sub. 3                                                                                ##STR193##    1.5063                       101                                                                               ##STR194##          CH.sub.3                                                                                 ##STR195##    1.5057                       102                                                                               ##STR196##          CH.sub.3                                                                                 ##STR197##    1.5070                       103                                                                               ##STR198##          CH.sub.3                                                                                 ##STR199##    1.4944                       104                                                                               ##STR200##          CH.sub.3                                                                                 ##STR201##    1.5067                       105                                                                               ##STR202##          CH.sub.3                                                                                 ##STR203##    1.5087                       106                                                                               ##STR204##          CH.sub.3                                                                                 ##STR205##    1.5076                       107                                                                               ##STR206##          CH.sub.3                                                                                 ##STR207##    1.5046                       108                                                                               ##STR208##          CH.sub.3                                                                                 ##STR209##    1.4948                       109                                                                               ##STR210##          CH.sub.3                                                                                 ##STR211##    1.4954                       110                                                                               ##STR212##          CH.sub.3                                                                                 ##STR213##    1.4962                       111                                                                               ##STR214##          CH.sub.3                                                                                 ##STR215##    1.4975                       112                                                                               ##STR216##          CH.sub.3                                                                                 ##STR217##    1.5110                       113                                                                               ##STR218##          CH.sub.3                                                                                 ##STR219##    1.5098                       114                                                                               ##STR220##          CH.sub.3                                                                                 ##STR221##    1.5031                       115                                                                               ##STR222##          CH.sub.3                                                                                 ##STR223##    1.4925                       116                                                                               ##STR224##          CH.sub.3                                                                                 ##STR225##    1.5044                       117                                                                               ##STR226##          CH.sub.3                                                                                 ##STR227##    1.5047                       118                                                                               ##STR228##          CH.sub.3                                                                                 ##STR229##    1.5040                       119                                                                               ##STR230##          CH.sub.3                                                                                 ##STR231##    1.5044                       120                                                                               ##STR232##          CH.sub.3                                                                                 ##STR233##    1.4912                       121                                                                               ##STR234##          CH.sub.3                                                                                 ##STR235##    1.4907                       122                                                                               ##STR236##          CH.sub.3                                                                                 ##STR237##    1.4930                       123                                                                               ##STR238##          CH.sub.3                                                                                 ##STR239##    1.4868                       124                                                                               ##STR240##          CH.sub.3                                                                                 ##STR241##    1.4873                       125                                                                               ##STR242##          CH.sub.3                                                                                 ##STR243##    1.4897                       126                                                                               ##STR244##          CH.sub.3                                                                                 ##STR245##    1.4841                       127                                                                               ##STR246##          CH.sub.3                                                                                 ##STR247##    1.4893                       128                                                                               ##STR248##          CH.sub.3                                                                                 ##STR249##    1.4864                       129                                                                               ##STR250##          CH.sub.3                                                                                 ##STR251##    1.4825                       130                                                                               ##STR252##          CH.sub.3                                                                                 ##STR253##    1.5118                       131                                                                               ##STR254##          CH.sub.3                                                                                 ##STR255##    1.4839                       132                                                                               ##STR256##          CH.sub.3                                                                                 ##STR257##    1.4919                       133                                                                               ##STR258##          CH.sub.3                                                                                 ##STR259##    1.5361                     134                                                                                 ##STR260##                                                                                         ##STR261##                                                                              ##STR262##    1.5214                       135                                                                               ##STR263##                                                                                         ##STR264##                                                                              ##STR265##    1.5148                       136                                                                               ##STR266##          C(CH.sub.3).sub.3                                                                        ##STR267##    1.5298                       137                                                                               ##STR268##          C(CH.sub.3).sub.3                                                                        ##STR269##    74                           138                                                                               ##STR270##          C(CH.sub.3).sub.3                                                                        ##STR271##    86-87                        139                                                                               ##STR272##          H                                                                                        ##STR273##    1.5222                       140                                                                               ##STR274##          CH.sub.3                                                                                 ##STR275##    1.5491                       141                                                                               ##STR276##          CH.sub.3                                                                                 ##STR277##    1.5626                       142                                                                               ##STR278##          CH.sub.3                                                                                 ##STR279##    1.5538                       143                                                                               ##STR280##          C(CH.sub.3).sub.3                                                                        ##STR281##    1.5171                       144                                                                               ##STR282##          CH.sub.3                                                                                 ##STR283##    1.4968                       145                                                                               ##STR284##                                                                                         ##STR285##                                                                              ##STR286##    1.5498                       146                                                                               ##STR287##          CH.sub.3                                                                                 ##STR288##    1.5091                       147                                                                               ##STR289##          C(CH.sub.3).sub.3                                                                        ##STR290##    1.5179                       148                                                                               ##STR291##          C(CH.sub.3).sub.3                                                                        ##STR292##    117                          149                                                                               ##STR293##          CH.sub.3                                                                                 ##STR294##    1.5187                       150                                                                               ##STR295##          CH.sub.3                                                                                 ##STR296##    1.5231                       151                                                                               ##STR297##                                                                                         ##STR298##                                                                              ##STR299##    1.5518                       152                                                                               ##STR300##                                                                                         ##STR301##                                                                              ##STR302##    1.5518                       153                                                                               ##STR303##                                                                                         ##STR304##                                                                              ##STR305##    1.5641                       154                                                                               ##STR306##          CH.sub.3                                                                                 ##STR307##    1.5366                       155                                                                               ##STR308##          H                                                                                        ##STR309##    1.5409                       156                                                                               ##STR310##          CH.sub.3                                                                                 ##STR311##    30                           157                                                                               ##STR312##          CH.sub.3                                                                                 ##STR313##    1.4599                       158                                                                               ##STR314##          CH.sub.3                                                                                 ##STR315##    1.5195                       159                                                                               ##STR316##          CH.sub.3                                                                                 ##STR317##    1.5361                       160                                                                               ##STR318##          t-C.sub.4 H.sub.9                                                                        ##STR319##    1.5366                       161                                                                               ##STR320##          i-C.sub.4H.sub.9                                                                         ##STR321##    1.5263                       162                                                                               ##STR322##          i-C.sub.4 H.sub.9                                                                        ##STR323##    1.5179                       163                                                                               ##STR324##          CH.sub.3                                                                                 ##STR325##    1.5445                       164                                                                               ##STR326##          CH.sub.3                                                                                 ##STR327##    1.5568                       165                                                                              CH.sub.3(CH.sub.2).sub.8                                                                           CH.sub.3                                                                                 ##STR328##    1.4461                       166                                                                              CH.sub.3(CH.sub.2).sub.8                                                                           CH.sub.3(CH.sub.2).sub.8                                                                 ##STR329##    01                           167                                                                               ##STR330##          CH.sub.3                                                                                 ##STR331##    1.4702                       168                                                                               ##STR332##          CH.sub.3                                                                                 ##STR333##    1.4921                       169                                                                               ##STR334##          CH.sub.3                                                                                 ##STR335##    1.5019                       170                                                                               ##STR336##          CH.sub.3                                                                                 ##STR337##    1.5034                       171                                                                               ##STR338##          CH.sub.3                                                                                 ##STR339##    1.5045                       172                                                                               ##STR340##          CH.sub.3                                                                                 ##STR341##    1.5040                       173                                                                               ##STR342##          CH.sub.3                                                                                 ##STR343##    1.5031                       174                                                                               ##STR344##          CH.sub.3                                                                                 ##STR345##    1.5000                       175                                                                               ##STR346##          CH.sub.3                                                                                 ##STR347##    1.5082                       176                                                                               ##STR348##          CH.sub.3                                                                                 ##STR349##    1.5079                       177                                                                               ##STR350##          CH.sub.3                                                                                 ##STR351##    1.5087                       178                                                                               ##STR352##          CH.sub.3                                                                                 ##STR353##    1.5095                       179                                                                               ##STR354##          CH.sub.3                                                                                 ##STR355##    1.5117                       180                                                                               ##STR356##          CH.sub.3                                                                                 ##STR357##    1.5060                       181                                                                               ##STR358##          t-C.sub.4 H.sub.9                                                                        ##STR359##    1.5072                       182                                                                               ##STR360##          CH.sub.3                                                                                 ##STR361##    1.5239                       183                                                                               ##STR362##          CH.sub.3                                                                                 ##STR363##    1.5212                       184                                                                               ##STR364##          CH.sub.3                                                                                 ##STR365##    1.5299                       185                                                                               ##STR366##          CH.sub.3                                                                                 ##STR367##    1.5282                       186                                                                               ##STR368##          CH.sub.3                                                                                 ##STR369##    1.5386                       187                                                                               ##STR370##          CH.sub.3                                                                                 ##STR371##    1.5506                       188                                                                               ##STR372##          CH.sub.3                                                                                 ##STR373##    1.5149                       189                                                                               ##STR374##          CH.sub.3                                                                                 ##STR375##    1.5086                       190                                                                               ##STR376##          CH.sub.3                                                                                 ##STR377##    1.5077                       191                                                                               ##STR378##          CH.sub.3                                                                                 ##STR379##    1.5108                       192                                                                               ##STR380##          CH.sub.3                                                                                 ##STR381##    1.5070                       193                                                                               ##STR382##          CH.sub.3                                                                                 ##STR383##    1.5028                       194                                                                               ##STR384##          CH.sub.3                                                                                 ##STR385##    1.5035                       195                                                                               ##STR386##          CH.sub.3                                                                                 ##STR387##    1.4978                       196                                                                               ##STR388##          CH.sub.3                                                                                 ##STR389##    1.5069                       197                                                                               ##STR390##          CH.sub.3                                                                                 ##STR391##    1.5061                       198                                                                               ##STR392##          CH.sub.3                                                                                 ##STR393##    1.5086                       199                                                                               ##STR394##          CH.sub.3                                                                                 ##STR395##    1.4929                       200                                                                               ##STR396##          CH.sub.3                                                                                 ##STR397##    1.5018                       201                                                                               ##STR398##          CH.sub.3                                                                                 ##STR399##    1.5003                       202                                                                               ##STR400##          CH.sub.3                                                                                 ##STR401##    1.4952                       203                                                                               ##STR402##          CH.sub.3                                                                                 ##STR403##    1.5356                       204                                                                               ##STR404##          CH.sub.3                                                                                 ##STR405##    1.5272                       205                                                                               ##STR406##          CH.sub.3                                                                                 ##STR407##    1.5241                       206                                                                               ##STR408##          CH.sub.3                                                                                 ##STR409##    130                          207                                                                               ##STR410##          CH.sub.3                                                                                 ##STR411##    1.5193                       208                                                                               ##STR412##          CH.sub.3                                                                                 ##STR413##    1.5375                       209                                                                               ##STR414##          CH.sub.3                                                                                 ##STR415##    1.5162                       210                                                                               ##STR416##          CH.sub.3                                                                                 ##STR417##    1.5321                       211                                                                               ##STR418##          CH.sub.3                                                                                 ##STR419##    1.5257                       212                                                                               ##STR420##          CH.sub.3                                                                                 ##STR421##    1.5269                       213                                                                               ##STR422##          CH.sub.3                                                                                 ##STR423##    1.5209                     __________________________________________________________________________    214                                                                                 ##STR424##          CH.sub.3                                                                                 ##STR425##    1.5185                       215                                                                               ##STR426##          CH.sub.3                                                                                 ##STR427##    1.5170                       216                                                                               ##STR428##          CH.sub.3                                                                                 ##STR429##    1.5034                       217                                                                               ##STR430##          CH.sub.3                                                                                 ##STR431##    1.5154                       218                                                                               ##STR432##          CH.sub.3                                                                                 ##STR433##                                 219                                                                               ##STR434##          CH.sub.3                                                                                 ##STR435##    1.5341                       220                                                                               ##STR436##          CH.sub.3                                                                                 ##STR437##    1.5249                       221                                                                               ##STR438##          CH.sub.3                                                                                 ##STR439##    1.5189                       222                                                                               ##STR440##          CH.sub.3                                                                                 ##STR441##    1.5177                       223                                                                               ##STR442##          CH.sub.3                                                                                 ##STR443##    1.5189                       224                                                                               ##STR444##          CH.sub.3                                                                                 ##STR445##    1.5177                       225                                                                               ##STR446##          CH.sub.3                                                                                 ##STR447##    1.5178                       226                                                                               ##STR448##          CH.sub.3                                                                                 ##STR449##    1.5126                       227                                                                               ##STR450##          CH.sub.3                                                                                 ##STR451##    1.5091                       228                                                                               ##STR452##          CH.sub.3                                                                                 ##STR453##    170                          229                                                                               ##STR454##          CH.sub.3                                                                                 ##STR455##    1.5170                       230                                                                               ##STR456##          CH.sub.3                                                                                 ##STR457##    1.5032                       231                                                                               ##STR458##          CH.sub.3                                                                                 ##STR459##    1.5111                       232                                                                               ##STR460##          CH.sub.3                                                                                 ##STR461##    1.5105                       233                                                                               ##STR462##          CH.sub.3                                                                                 ##STR463##    1.5072                       234                                                                               ##STR464##          CH.sub.3                                                                                 ##STR465##    1.5049                       235                                                                               ##STR466##          CH.sub.3                                                                                 ##STR467##    b.p. 160°                                                              C./0.1                       236                                                                               ##STR468##          H                                                                                        ##STR469##    1.5433                       237                                                                               ##STR470##          H                                                                                        ##STR471##    1.5601                       238                                                                               ##STR472##          CH.sub.3                                                                                 ##STR473##    b.p. 200°                                                              C./0.3                       239                                                                               ##STR474##          CH.sub.3                                                                                 ##STR475##    b.p. 190°                                                              C./0.2                       240                                                                               ##STR476##          CH.sub.3                                                                                 ##STR477##    1.5092                       241                                                                               ##STR478##          CH.sub.3                                                                                 ##STR479##    1.5062                       242                                                                               ##STR480##          CH.sub.3                                                                                 ##STR481##    1.5076                       243                                                                               ##STR482##          CH.sub.3                                                                                 ##STR483##    1.5039                       244                                                                               ##STR484##          CH.sub.3                                                                                 ##STR485##    1.5047                       245                                                                               ##STR486##          CH.sub.3                                                                                 ##STR487##    1.5067                       246                                                                               ##STR488##          C(CH.sub.3).sub.3                                                                        ##STR489##    1.5042                       247                                                                               ##STR490##          C(CH.sub.3).sub.3                                                                        ##STR491##    1.4987                       248                                                                               ##STR492##          CH.sub.3                                                                                 ##STR493##    1.5073                       249                                                                               ##STR494##          CH.sub.3                                                                                 ##STR495##    1.4995                       250                                                                               ##STR496##          CH.sub.3                                                                                 ##STR497##    1.5073                       251                                                                               ##STR498##          CH.sub.3                                                                                 ##STR499##    1.4995                       252                                                                               ##STR500##          CH.sub.3                                                                                 ##STR501##    1.4970                       253                                                                               ##STR502##          CH.sub.3                                                                                 ##STR503##                                 254                                                                               ##STR504##          CH.sub.3                                                                                 ##STR505##    1.5105                       255                                                                               ##STR506##          CH.sub.3                                                                                 ##STR507##    1.5016                       256                                                                               ##STR508##          CH.sub. 3                                                                                ##STR509##    1.5076                       257                                                                               ##STR510##          CH.sub.3                                                                                 ##STR511##    1.5044                       258                                                                               ##STR512##          CH.sub.3                                                                                 ##STR513##    1.5064                       259                                                                               ##STR514##          CH.sub.3                                                                                 ##STR515##    1.5023                       260                                                                               ##STR516##          CH.sub.3                                                                                 ##STR517##    1.5092                       261                                                                               ##STR518##          CH.sub.3                                                                                 ##STR519##    oil                          262                                                                               ##STR520##          CH.sub.3                                                                                 ##STR521##    oil                          263                                                                               ##STR522##          CH.sub.3                                                                                 ##STR523##    oil                          264                                                                               ##STR524##          CH.sub.3                                                                                 ##STR525##    oil                          265                                                                               ##STR526##          CH.sub.3                                                                                 ##STR527##    1.5110                       266                                                                               ##STR528##          CH.sub.3                                                                                 ##STR529##    1.5042                       267                                                                               ##STR530##          CH.sub.3                                                                                 ##STR531##    1.5067                       268                                                                               ##STR532##          CH.sub.3                                                                                 ##STR533##    1.5047                       269                                                                               ##STR534##          CH.sub.3                                                                                 ##STR535##    1.5071                       270                                                                               ##STR536##          CH.sub.3                                                                                 ##STR537##    1.5085                       271                                                                               ##STR538##          CH.sub.3                                                                                 ##STR539##    1.5043                       272                                                                               ##STR540##          CH.sub.3                                                                                 ##STR541##    1.5061                       273                                                                               ##STR542##          CH.sub.3                                                                                 ##STR543##    1.5039                       274                                                                               ##STR544##          CH.sub.3                                                                                 ##STR545##    1.5049                       275                                                                               ##STR546##          CH.sub.3                                                                                 ##STR547##    1.5064                       276                                                                               ##STR548##          CH.sub.3                                                                                 ##STR549##    1.5051                       277                                                                               ##STR550##          CH.sub.3                                                                                 ##STR551##    1.5047                       278                                                                               ##STR552##          CH.sub.3                                                                                 ##STR553##    1.5067                       279                                                                               ##STR554##          CH.sub.3                                                                                 ##STR555##    b.p. 210°                                                              C./0.1                       280                                                                               ##STR556##          CH.sub.3                                                                                 ##STR557##    b.p. 210°                                                              C./0.2                       281                                                                               ##STR558##          CH.sub.3                                                                                 ##STR559##    1.5027                       282                                                                               ##STR560##          CH.sub.3                                                                                 ##STR561##    1.5041                       283                                                                               ##STR562##          CH.sub.3                                                                                 ##STR563##    1.5422                       284                                                                               ##STR564##          CH.sub.3                                                                                 ##STR565##    1.5457                       285                                                                               ##STR566##          CH.sub.3                                                                                 ##STR567##    1.5305                       286                                                                               ##STR568##          CH.sub.3                                                                                 ##STR569##    1.5269                       287                                                                               ##STR570##          CH.sub.3                                                                                 ##STR571##    1.5346                       288                                                                               ##STR572##          CH.sub.3                                                                                 ##STR573##    1.5340                       289                                                                               ##STR574##          CH.sub.3                                                                                 ##STR575##    b.p. 220°                                                              C./0.2                       290                                                                               ##STR576##          CH.sub.3                                                                                 ##STR577##    1.5293                       291                                                                               ##STR578##          CH.sub.3                                                                                 ##STR579##    1.5286                       292                                                                               ##STR580##          CH.sub.3                                                                                 ##STR581##    1.5251                       293                                                                               ##STR582##          CH.sub.3                                                                                 ##STR583##    1.5150                       294                                                                               ##STR584##          CH.sub.3                                                                                 ##STR585##    1.5133                       295                                                                               ##STR586##          CH.sub.3                                                                                 ##STR587##    1.5064                       296                                                                               ##STR588##          CH.sub.3                                                                                 ##STR589##    1.5082                       297                                                                               ##STR590##          CH.sub.3                                                                                 ##STR591##    1.5090                       298                                                                               ##STR592##          CH.sub.3                                                                                 ##STR593##    1.5076                       299                                                                               ##STR594##          CH.sub.3                                                                                 ##STR595##    1.5045                       300                                                                               ##STR596##          CH.sub.3                                                                                 ##STR597##    1.5089                       301                                                                               ##STR598##          CH.sub. 3                                                                                ##STR599##    1.5062                       302                                                                               ##STR600##          CH.sub.3                                                                                 ##STR601##    1.5021                       303                                                                               ##STR602##          CH.sub.3                                                                                 ##STR603##    1.5171                       304                                                                               ##STR604##          CH.sub.3                                                                                 ##STR605##    1.5085                       305                                                                               ##STR606##          CH.sub.3                                                                                 ##STR607##                                 306                                                                               ##STR608##          CH.sub.3                                                                                 ##STR609##    1.4995                       307                                                                               ##STR610##          CH.sub.3                                                                                 ##STR611##    1.4909                       308                                                                               ##STR612##          CH.sub.3                                                                                 ##STR613##    1.4908                       309                                                                               ##STR614##          CH.sub.3                                                                                 ##STR615##    1.5002                       310                                                                               ##STR616##          CH.sub.3                                                                                 ##STR617##    1.4980                       311                                                                               ##STR618##          CH.sub.3                                                                                 ##STR619##    1.4941                       312                                                                               ##STR620##          CH.sub.3                                                                                 ##STR621##    1.4953                       313                                                                               ##STR622##          CH.sub.3                                                                                 ##STR623##    1.4939                       314                                                                               ##STR624##          CH.sub.3                                                                                 ##STR625##    1.4902                       315                                                                               ##STR626##          CH.sub.3                                                                                 ##STR627##    1.4900                       316                                                                               ##STR628##          CH.sub.3                                                                                 ##STR629##    1.4979                       317                                                                               ##STR630##          CH.sub.3                                                                                 ##STR631##    1.4905                       318                                                                               ##STR632##          CH.sub.3                                                                                 ##STR633##    1.5041                       319                                                                               ##STR634##          CH.sub.3                                                                                 ##STR635##    1.5058                       320                                                                               ##STR636##          CH.sub.3                                                                                 ##STR637##    1.5068                       321                                                                               ##STR638##          CH.sub.3                                                                                 ##STR639##    1.5031                       322                                                                               ##STR640##          CH.sub.3                                                                                 ##STR641##    1.5021                       323                                                                               ##STR642##          CH.sub.3                                                                                 ##STR643##    1.5012                       324                                                                               ##STR644##          CH.sub.3                                                                                 ##STR645##    1.4984                       325                                                                               ##STR646##          CH.sub.3                                                                                 ##STR647##    1.5069                       326                                                                               ##STR648##          CH.sub.3                                                                                 ##STR649##    oil                          327                                                                               ##STR650##          CH.sub.3                                                                                 ##STR651##    oil                          328                                                                               ##STR652##          CH.sub.3                                                                                 ##STR653##    oil                          329                                                                               ##STR654##          CH.sub.3                                                                                 ##STR655##    oil                          330                                                                               ##STR656##          CH.sub.3                                                                                 ##STR657##    oil                          331                                                                               ##STR658##          CH.sub.3                                                                                 ##STR659##    oil                          332                                                                               ##STR660##          CH.sub.3                                                                                 ##STR661##                                 333                                                                               ##STR662##          CH.sub.3                                                                                 ##STR663##                                 334                                                                               ##STR664##          CH.sub.3                                                                                 ##STR665##                                 335                                                                               ##STR666##          CH.sub.3                                                                                 ##STR667##                                 336                                                                               ##STR668##          CH.sub.3                                                                                 ##STR669##                                 337                                                                               ##STR670##          CH.sub.3                                                                                 ##STR671##                                 338                                                                               ##STR672##          CH.sub.3                                                                                 ##STR673##                                 339                                                                               ##STR674##          CH.sub.3                                                                                 ##STR675##                                 340                                                                               ##STR676##          CH.sub.3                                                                                 ##STR677##                                 341                                                                               ##STR678##          CH.sub.3                                                                                 ##STR679##                                 342                                                                               ##STR680##          CH.sub.3                                                                                 ##STR681##                                 343                                                                               ##STR682##          CH.sub.3                                                                                 ##STR683##                                 344                                                                               ##STR684##          CH.sub.3                                                                                 ##STR685##                                 345                                                                               ##STR686##          CH.sub.3                                                                                 ##STR687##                                 346                                                                               ##STR688##          CH.sub.3                                                                                 ##STR689##                                 347                                                                               ##STR690##          CH.sub.3                                                                                 ##STR691##                                 348                                                                               ##STR692##          CH.sub.3                                                                                 ##STR693##                                 349                                                                               ##STR694##          CH.sub.3                                                                                 ##STR695##                                 350                                                                               ##STR696##          CH.sub.3                                                                                 ##STR697##                                 -351                                                                              ##STR698##          CH.sub.3                                                                                 ##STR699##                                 352                                                                               ##STR700##          CH.sub.3                                                                                 ##STR701##                                 353                                                                               ##STR702##          CH.sub.3                                                                                 ##STR703##                                 354                                                                               ##STR704##          CH.sub.3                                                                                 ##STR705##                                 355                                                                               ##STR706##          CH.sub.3                                                                                 ##STR707##                                 356                                                                               ##STR708##          CH.sub.3                                                                                 ##STR709##                                 357                                                                               ##STR710##          CH.sub.3                                                                                 ##STR711##                                 358                                                                               ##STR712##          CH.sub.3                                                                                 ##STR713##                                 359                                                                               ##STR714##          CH.sub. 3                                                                                ##STR715##                                 360                                                                               ##STR716##          CH.sub.3                                                                                 ##STR717##                                 361                                                                               ##STR718##          CH.sub.3                                                                                 ##STR719##                                 362                                                                               ##STR720##          CH.sub.3                                                                                 ##STR721##                                 363                                                                               ##STR722##          CH.sub.3                                                                                 ##STR723##                                 364                                                                               ##STR724##          CH.sub.3                                                                                 ##STR725##                                 365                                                                               ##STR726##          CH.sub.3                                                                                 ##STR727##                                 366                                                                               ##STR728##          CH.sub.3                                                                                 ##STR729##                                 367                                                                               ##STR730##          CH.sub.3                                                                                 ##STR731##                                 368                                                                               ##STR732##          CH.sub.3                                                                                 ##STR733##                                 369                                                                               ##STR734##          CH.sub.3                                                                                 ##STR735##                                 370                                                                               ##STR736##          CH.sub.3                                                                                 ##STR737##                                 371                                                                               ##STR738##          CH.sub.3                                                                                 ##STR739##                                 372                                                                               ##STR740##          CH.sub.3                                                                                 ##STR741##                                 373                                                                               ##STR742##          CH.sub.3                                                                                 ##STR743##                                 374                                                                               ##STR744##          CH.sub.3                                                                                 ##STR745##                                 375                                                                               ##STR746##          CH.sub.3                                                                                 ##STR747##                                 376                                                                               ##STR748##          CH.sub.3                                                                                 ##STR749##                                 377                                                                               ##STR750##          CH.sub.3                                                                                 ##STR751##                                 378                                                                               ##STR752##          CH.sub.3                                                                                 ##STR753##                                 379                                                                               ##STR754##          CH.sub.3                                                                                 ##STR755##                                 380                                                                               ##STR756##          CH.sub.3                                                                                 ##STR757##                                 381                                                                               ##STR758##          CH.sub.3                                                                                 ##STR759##                                 382                                                                               ##STR760##          CH.sub.3                                                                                 ##STR761##                                 383                                                                               ##STR762##          CH.sub.3                                                                                 ##STR763##                                 384                                                                               ##STR764##          CH.sub.3                                                                                 ##STR765##                                 385                                                                               ##STR766##          CH.sub.3                                                                                 ##STR767##                                 386                                                                               ##STR768##          CH.sub.3                                                                                 ##STR769##                                 387                                                                               ##STR770##          CH.sub.3                                                                                 ##STR771##                                 388                                                                               ##STR772##          CH.sub.3                                                                                 ##STR773##                                 389                                                                               ##STR774##          CH.sub.3                                                                                 ##STR775##                                 390                                                                               ##STR776##          CH.sub.3                                                                                 ##STR777##                                 391                                                                               ##STR778##          CH.sub.3                                                                                 ##STR779##                                 392                                                                               ##STR780##          CH.sub.3                                                                                 ##STR781##                                 393                                                                               ##STR782##          CH.sub.3                                                                                 ##STR783##                                 394                                                                               ##STR784##          CH.sub.3                                                                                 ##STR785##                                 395                                                                               ##STR786##          CH.sub.3                                                                                 ##STR787##                                 396                                                                               ##STR788##          CH.sub.3                                                                                 ##STR789##                                 397                                                                               ##STR790##          CH.sub.3                                                                                 ##STR791##                                 398                                                                               ##STR792##          CH.sub.3                                                                                 ##STR793##                                 399                                                                               ##STR794##          CH.sub.3                                                                                 ##STR795##                                 400                                                                               ##STR796##          CH.sub.3                                                                                 ##STR797##                                 401                                                                               ##STR798##          CH.sub.3                                                                                 ##STR799##                                 402                                                                               ##STR800##          CH.sub.3                                                                                 ##STR801##                                 403                                                                               ##STR802##          CH.sub.3                                                                                 ##STR803##                                 404                                                                               ##STR804##          CH.sub.3                                                                                 ##STR805##                                 405                                                                               ##STR806##          CH.sub.3                                                                                 ##STR807##                                 406                                                                               ##STR808##          CH.sub.3                                                                                 ##STR809##                                 407                                                                               ##STR810##          CH.sub.3                                                                                 ##STR811##                                 408                                                                               ##STR812##          CH.sub.3                                                                                 ##STR813##                                 409                                                                               ##STR814##          CH.sub.3                                                                                 ##STR815##                                 410                                                                               ##STR816##          CH.sub.3                                                                                 ##STR817##                                 411                                                                               ##STR818##          CH.sub.3                                                                                 ##STR819##                                 412                                                                               ##STR820##          CH.sub.3                                                                                 ##STR821##                                 413                                                                               ##STR822##          CH.sub.3                                                                                 ##STR823##                                 414                                                                               ##STR824##          CH.sub.3                                                                                 ##STR825##                                 415                                                                               ##STR826##          CH.sub.3                                                                                 ##STR827##                                 416                                                                               ##STR828##          CH.sub.3                                                                                 ##STR829##                                 417                                                                               ##STR830##          CH.sub.3                                                                                 ##STR831##                                 418                                                                               ##STR832##          CH.sub.3                                                                                 ##STR833##                                 419                                                                               ##STR834##          CH.sub.3                                                                                 ##STR835##                                 420                                                                               ##STR836##          CH.sub.3                                                                                 ##STR837##                                 421                                                                               ##STR838##          CH.sub.3                                                                                 ##STR839##                                 422                                                                               ##STR840##          CH.sub.3                                                                                 ##STR841##    1.4986                       423                                                                               ##STR842##          CH.sub.3                                                                                 ##STR843##    1.5002                     __________________________________________________________________________

USE EXAMPLES

In the fungicidal use examples which follow, the compounds indicatedbelow are employed as comparative substances. ##STR844##

EXAMPLE A

Phytophthora test (tomato)/protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dripping wet. After the spraycoating has dried on, the plants are inoculated with an aqueous sporesuspension of Phytophthora infestans.

The plants are placed in an incubation cabinet 100% relative atmospherichumidity and at about 20° C.

Evaluation is carried out 3 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples: 71 and 78.

                                      TABLE A                                     __________________________________________________________________________    Phytophthora test (tomato)/protective                                                                         Infestation in % of an                                                        active compound concen-                       Active compound                 tration of 0.005%                             __________________________________________________________________________     ##STR845##                     60                                              (known)                                                                      ##STR846##                     16                                              × HCl                                                                  ##STR847##                     21                                            __________________________________________________________________________

EXAMPLE B

Drechslera graminea test (barley)/seed treatment (syn. Helminthosporiumgramineum)

The active compounds are used as dry dressings. These are prepared byextending the particular active compound with a ground mineral to give afinely pulverulent mixture, which ensures uniform distribution on theseed surface.

To apply the dressing, the infected seed is shaken with the dressing ina closed glass flask for 3 minutes.

The seed is embedded in sieved, moist standard soil and is exposed to atemperature of 4° C. in closed Petri dishes in a refrigerator for 10days. Germination of the barley, and possibly also of the fungus spores,is thereby initiated. 2 batches of 50 grains of the pregerminated barleyare subsequently sown 3 cm deep in standard soil and are cultivated in agreenhouse at a temperature of about 18° C., in seedboxes which areexposed to light for 15 hours daily.

About 3 weeks after sowing, the plants are evaluated for symptoms ofstripe disease.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples: 71, 74, 77, 98 and 104.

                                      TABLE B                                     __________________________________________________________________________    Drechslera graminea test (barley)/seed treatment                              (syn. Helminthosporium gramineum)                                                                                Amount of                                                                              Diseased plants                                                      active compound                                                                        as % of the                                                          used in mg/kg                                                                          total plants                      Active compound                    of seed  emerged                           __________________________________________________________________________    untreated                                   24.0                               ##STR848##                        600      19.0                                (known)                                                                      ##STR849##                        500      1.1                                ##STR850##                        500      1.2                                ##STR851##                        500      3.5                                ##STR852##                        500      2.5                                ##STR853##                        500      3.6                               __________________________________________________________________________

EXAMPLE C

Erysiphe test (barley)/protective

Solvent: 100 parts by weight of dimethylformamide

Emulsifier: 0.25 parts by weight of alkylaryl polygylcol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound until dew-moist. After the spray coatinghas dried on, the plants are dusted with spores of Erysiphe graminisif.sp. hordei.

the plants are placed in a greenhouse at a temperature of about 25° C.and a relative atmospheric humidity of about 80%, in order to promotethe development of powdery mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, a clearly superior activity compared with the prior art isshown, for example, by the compounds according to the followingpreparation examples: 29, 71, 72, 73, 74, 75, 76, 78, 89, 90, 92, 94,95, 97, 98, 100, 102, 104, 105, 106, 107, 113.

                                      TABLE C                                     __________________________________________________________________________    Erysiphe test (barley)/protective                                                                             Active compound                                                                        Disease                                                              concentration                                                                          infestation                                                          in the spray                                                                           as % of the                                                          liquor in %                                                                            untreated                            Active compound                 by weight                                                                              control                              __________________________________________________________________________     ##STR854##                     0.025    100                                   ##STR855##                     0.025    3.8                                   ##STR856##                     0.025    3.8                                   ##STR857##                     0.025    25.0                                  ##STR858##                     0.025    12.5                                  ##STR859##                     0.025    12.5                                  ##STR860##                     0.025    25.0                                  ##STR861##                     0.025    12.5                                  ##STR862##                     0.025    12.5                                  ##STR863##                     0.025    0.0                                   ##STR864##                     0.025    25.0                                  ##STR865##                     0.025    12.5                                  ##STR866##                     0.025    8.8                                   ##STR867##                     0.025    12.5                                  ##STR868##                     0.025    16.3                                  ##STR869##                     0.025    10.0                                  ##STR870##                     0.025    3.8                                   ##STR871##                     0.025    12.5                                  ##STR872##                     0.025    12.5                                  ##STR873##                     0.025    33.8                                  ##STR874##                     0.025    21.3                                  ##STR875##                     0.025    12.5                                  ##STR876##                     0.025    33.8                                 __________________________________________________________________________

END

We claim:
 1. A method of combating fungi which comprises applying tosuch fungi or to a fungus habitat a fungicidally effective amount of asubstituted aminoketal of the formula ##STR877## in which R¹ representsoptionally substituted alkyl, or represents alkenyl and alkinyl, oroptionally substituted cycloalkyl, optionally substituted aralkenyl oroptionally substituted aryl,R² has the same meaning as R¹ andfurthermore may represent hydrogen and R³ and R⁴, together with thenitrogen atom to which they are bonded, represent an optionallysubstituted pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl,perhydroazepinyl, or pyrazolyl radical,or a physiologically toleratedaddition product thereof with an acid or metal salt.
 2. A processaccording to claim 1, in whichR¹ represents straight-chain or branchedalkyl having 1 to 18 carbon atoms; straight-chain or branchedhalogenoalkyl having 1 to 12 carbon atoms and 1 to 5 halogen atoms,straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in thealkyl part, aralkyl, aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphinylalkyl and arylsulphonylalkyl, each having 1 to 6 carbonatoms in each alkyl part and 6 to 10 carbon atoms in the aryl part, theradicals in each case being optionally monosubstituted orpolysubstituted by identical or different substituents, the followingbeing suitable aryl substituents in each case: halogen, cyano, nitro,alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms;halogenoalkyl, halogenoalkoxy, halogenoalkylthio, each having 1 or 2carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, andphenoxy or phenyl which is optionally substituted by halogen, or byalkyl having 1 to 4 carbon atoms; and represents cycloalkylalkyl having1 to 4 carbon atoms in the alkyl part and 3 to 7 carbon atoms in thecycloalkyl part which is optionally monosubstituted or polysubstitutedby alkyl having 1 to 4 carbon atoms, and also represents straight-chainor branched alkenyl or alkinyl, each having 2 to 6 carbon atoms,cycloalkyl which has 3 to 7 carbon atoms and is optionallymonosubstituted or polysubstituted by identical or different alkylradicals having 1 to 4 carbon atoms, or represents aryl having 6 to 10carbon atoms and arylalkenyl having 2 to 6 carbon atoms in the alkenylpart and 6 to 10 carbon atoms in the aryl part, each of which isoptionally monosubstituted or polysubstituted by identical or differentsubstituents, suitable aryl substituents in each case being: halogen,cyano, nitro; alkyl, alkoxy, alkylthio, each having 1 to 4 carbon atoms;halogenoalkyl, halogenoalkoxy, halogenoalkylthio, each having 1 or 2carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, andphenoxy or phenyl which is optionally substituted by halogen, inparticular fluorine or chlorine, or by alkyl having 1 to 4 carbon atoms;R² has the meaning of R¹ and many be identical or different to thisradical, and additionally represents hydrogen, the optional substituentson the heterocyclic radical made up of R³ and R⁴ being alkyl having 1 to4 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkylpart and phenyl.
 3. A process according to claim 1 in whichR¹ representsstraight-chain or branched alkyl having 1 to 12 carbon atoms,cyclopropyl, cyclopentyl, cyclohexyl, straight-chain or branchedhalogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, orphenyl, phenylalkyl, phenoxyalkyl, benzyloxyalkyl, phenylthioalkyl,phenylsulphinylalkyl and phenylsulphonylalkyl, each having 1 to 5 carbonatoms in the alkyl part, the radicals in each case being optionallymonosubstituted, disubstituted or trisubstituted by identical ordifferent substituents, and phenylalkenyl which has 2 to 4 carbon atomsin the alkenyl part and is optionally monosubstituted, disubstituted ortrisubstituted by identical or different substituents, preferred phenylsubstituents being: fluorine, chlorine, bromine, cyano, nitro, methyl,methoxy, methylthio, ethyl, ethoxy, ethylthio, n- and i-propyl,isopropoxy, n-, iso-, sec.- and t-butyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, cyclohexyl, methoxycarbonyl,ethoxycarbonyl and phenoxy or phenyl which is optionally substituted byfluorine, chlorine or methyl; and R² represents straight-chain orbranched alkyl having 1 to 10 carbon atoms, benzyl and phenyl which isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents, phenyl or benzyl substituents in each casebeing: fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, methoxycarbonyl andethoxycarbonyl, or represents cyclopropyl, cyclopentyl and cyclohexyl,the optional substituents on the heterocyclic radical made up of R³ andR⁴ comprising up to three substituents selected from the groupconsisting of methyl, ethyl, n- or i-propyl, phenyl, methoxy-carbonyland ethoxycarbonyl.
 4. A process according to claim 3, in whichR¹represents straight-chain or branched alkyl having 1 to 5 carbon atoms,and phenylalkenyl, phenylalkyl, phenoxyalkyl, benzyloxyalkyl,phenylthioalkyl, phenylsulphinylalkyl and phenylsulphonylalkyl, each ofwhich has up to 5 carbon atoms in the alkyl part or alkenyl part and isoptionally monosubstituted, disubstituted or trisubstituted by identicalor different substituents, the following being mentioned as phenylsubstituents: fluorine, chlorine, bromine, methyl, ethyl, n- andi-propyl, t-butyl-, methoxy, ethoxy, isopropoxy, cyclohexyl,trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, nitro, cyano, phenyl and phenoxy; and R² representsstraight-chain or branched alkyl having 1 to 4 carbon atoms or hydrogen.5. A process according to claim 1, in whichR¹ represents the groupings##STR878## R⁵ represents phenyl, phenoxy, phenylthio, phenylsulphinyl orphenylsulphonyl, each of which is optionally monosubstituted totrisubstituted by identical or different substituents, the followingbeing mentioned as substituents: fluorine, chlorine, bromine, nitro,cyclohexyl, straight-chain or branched alkyl having 1 to 4 carbon atoms,straight-chain or branched alkoxy having 1 to 3 carbon atoms andalkoxycarbonyl having 1 or 2 carbon atoms in the alkoxy part, R²represents a straight-chain or branched alkyl having 1 to 4 carbonatoms, the optional substituents on the heterocyclic radical made up ofR³ and R⁴ being alkyl radicals having 1 to 3 carbon atoms.
 6. A processaccording to claim 5, in whichR¹ represents the groupings ##STR879##wherein R⁶ represents phenyl which is in each case optionallymonosubstituted to trisubstituted by identical or differentsubstituents, the following being mentioned as substituents: fluorine,chlorine, bromine, nitro, cyclohexyl, straight-chain or branched alkylor alkoxy, each having 1 or 2 carbon atoms in the alkyl part, and R²represents straight-chain or branched alkyl having 1 to 4 carbon atoms.7. A process according to claim 1, wherein such compoundis2-(4-chlorophenoxy-t-butyl)-2-methyl-4-(piperidin-1-ylmethyl)-1,3-dioxolane2-(2,4-dichlorophenyl-t-butyl)-2-methyl-4-(3-methylpiperidin-1-ylmethyl)-1,3-dioxolane,2-(2-ethylphenoxy-t-butyl)-2-methyl-4-(3-methyl-piperidin-1-ylmethyl)-1,3-dioxolane,or 4-(3,5-dimethyl-piperidin-1-ylmethyl)-1,3-dioxolane, or aphysiologically tolerated addition product thereof with an acid or metalsalt.
 8. A substituted aminoketal of the formula ##STR880## in whichR^(1') represents a straight-chain or branched alkyl having 6 to 18carbon atoms; straight-chain or branched branched halogenoalkyl having 2to 12 carbon atoms and 1 to 5 halogen atoms, straight-chain orcyanoalkyl having 1 to 4 carbon atoms in the alkyl part, benzyl which ismonosubstituted or polysubstituted by identical or differentsubstituents, arylalkyl which has 2 to 6 carbon atoms in the alkyl partand 6 to 10 carbon atoms in the aryl part and is optionallymonosubstituted or polysubstituted by identical or differentsubstituents, and aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphonylalkyl and arylsulphonylalkyl, each of which has 1 to 6carbon atoms in each alkyl part and 6 to 10 carbon atoms in the arylpart, the aryl substituents in each case being:halogen, cyano, nitro;alkyl, alkoxy and alkylthio, each having 1 to 4 carbon atoms,halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbonatoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, andphenoxy or phenyl which is optionally substituted by halogen, or byalkyl having 1 to 4 carbon atoms; cycloalkylalkyl having 1 to 4 carbonatoms in the alkyl part and 3 to 7 carbon atoms in the cycloalkyl partwhich is optionally monosubstituted or polysubstituted by alkyl having 1to 4 carbon atoms; and also represents straight-chain or branchedalkenyl having 2 to 5 carbon atoms, straight-chain or branched alkinylhaving 2 to 6 carbon atoms; cycloalkyl which has 3 to 7 carbon atoms andis monosubstituted or polysubstituted by identical or different alkylradicals having 1 to 4 carbon atoms, and represents arylalkenyl having 2to 6 carbon atoms in the alkenyl part and 6 to 10 carbon atoms in thearyl part, the aryl substituents in each case being: halogen, cyano,nitro; alkyl, alkoxy and alkylthio, each having 1 or 2 carbon atoms and1 to 5 halogen atoms, cycloalkyl having 5 to 7 carbon atoms,alkoxycarbonyl having 1 to 4 carbon atoms in the alkyl part, phenoxy orphenyl which is optionally substituted by halogen, or by alkyl having 1to 4 carbon atoms; R^(2') represents hydrogen, straight-chain orbranched alkyl having 1 to 18 carbon atoms, straight-chain or branchedhalogenoalkyl having 1 to 12 carbon atoms and 1 to 5 halogen atoms,straight-chain or branched cyanoalkyl having 1 to 4 carbon atoms in thealkyl part, arylalkyl, aryloxyalkyl, aralkyloxyalkyl, arylthioalkyl,arylsulphinylalkyl, and arylsulphonylalkyl, each of which has 1 to 6carbon atoms in each alkyl part and 6 to 10 carbon atoms in the arylpart and is optionally monosubstituted or polysubstituted by identicalor different substituents, the aryl substituents in each case being:halogen, cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 to 4carbon atoms; halogenoalkyl, halogenoalkoxy and halogenoalkylthio, eachhaving 1 or 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5to 7 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in thealkyl part, and phenoxy or phenyl which is optionally substituted byhalogen, in particular fluorine or chlorine, or by alkyl having 1 to 4carbon atoms; and cycloalkylalkyl having 1 to 4 carbon atoms in thealkyl part and 3 to 7 carbon atoms in the cycloalkyl part which isoptionally monosubstituted polysubstituted by alkyl having 1 to 4 carbonatoms, and also represents straight-chain or branched alkenyl oralkinyl, each having 2 to 6 carbon atoms, cycloalkyl which has 3 to 7carbon atoms and is optionally monosubstituted or polysubstituted byidentical or different alkyl radicals having 1 to 4 carbon atoms, orrepresents aryl having 6 to 10 carbon atoms and arylalkenyl having 2 to6 carbon atoms in the alkenyl part and 6 to 10 carbon atoms in the arylpart, each of which is optionally monosubstituted or poly-substituted byidentical or different substituents, the aryl substituents being:halogen, cyano, nitro; alkyl, alkoxy and alkylthio, each having 1 to 4carbon atoms; halogenoalkyl, halogenoalkoxy and halogenoalkylthio, eachhaving 1 to 2 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 5to 7 carbon atoms, alkoxycarbonyl having 1 to 4 carbon atoms in thealkyl part, and phenoxy or phenyl which is optionally substituted byhalogen or by alkyl having 1 to 4 carbon atoms or by alkyl having 1 to 4carbon atoms, R^(3') and R^(4'), together with the nitrogen atom towhich they are bonded, represent a pyrrolidinyl, piperidinyl,piperazinyl, morpholinyl, perhydrozepinyl or pyrazolyl radical which isoptionally substituted by at least one substituent selected from thegroup consisting of alkyl having 1 to 4 carbon atoms, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkyl part, and phenyl.
 9. Asubstituted aminoketal according to claim 8, in whichR^(1') representsstraight-chain or branched alkyl having 6 to 12 carbon atoms;straight-chain or branched halogenoalkyl having 2 to 6 carbon atoms and1 to 5 halogen atoms, cyanomethyl or cyanoethyl, benzyl which ismonosubstituted to trisubstituted by identical or differentsubstituents, phenylalkyl which has 2 to 6 carbon atoms in the alkylpart and is optionally monosubstituted to trisubstituted by identical ordifferent substituents, and phenoxyalkyl, phenylalkoxyalkyl,phenylthioalkyl, phenylsulphinylalkyl and phenylsulphonylalkyl, each ofwhich has 1 to 4 carbon atoms in each alkyl part, the phenyl or benzylsubstituents in each case being: fluorine, chlorine, bromine, cyano,nitro, methyl, methoxy, methylthio, ethyl, ethoxy, ethylthio, n- andi-propyl, isopropoxy, n-, iso-, sec.- and t-butyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, cyclohexyl, methoxycarbonyl andethoxycarbonyl, and phenoxy or phenyl which is optionally substituted byfluorine, chlorine or methyl; and also represents cycloalkylalkyl having1 to 4 carbon toms in the alkyl part and 5 to 7 carbon atoms in thecycloalkyl part which is optionally monosubstituted or polysubstitutedby alkyl having 1 to 4 carbon atoms; and also represents straight-chainor branched alkenyl having 3 to 5 carbon atoms, straight-chain orbranched alkinyl having 3 to 6 carbon atoms; cycloalkyl which has 5 to 7carbon atoms and is monosubstituted to trisubstituted by identical ordifferent substituents from amongst methyl, ethyl or propyl, andrepresents phenylalkenyl having 2 to 5 carbon atoms in the alkenyl part,the phenyl substituents in each case being: fluorine, chlorine, bromine,cyano, nitro, methyl, methoxy, methylthio, ethyl, ethoxy, ethylthio, n-and i-propyl, isopropoxy, n-, iso-, sec.- and t-butyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, cyclohexyl, methoxycarbonyl andethoxycarbonyl, and phenoxy or phenyl which is optionally substituted byfluorine, chlorine or methyl; R^(2') represents hydrogen, straight-chainor branched alkyl having 1 to 10 carbon atoms; and benzyl or phenylwhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents, the phenyl or benzyl substituents in each casebeing: fluorine, chlorine, bromine, cyano, nitro, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, methoxycarbonyl andethoxycarbonyl, and R^(3') and R^(4'), together with the nitrogen atomto which they are bonded, represent pyrrolidin-1-yl, piperidin-1-yl,piperazin-1-yl, morpholin-4-yl, perhydroazepin-1-yl, or pyrazol-1-yl,each of which is optionally monosubstituted to trisubstituted byidentical or different substituents, the following being mentioned assubstituents: methyl, ethyl, n- and i-propyl, phenyl, methoxycarbonyland ethoxycarbonyl.
 10. A substituted aminoketal according to claim 8,in whichR^(1') represents the groupings ##STR881## wherein R⁵ representsphenyl, phenoxy, phenylthio, phenylsulphinyl or phenylsulphonyl, each ofwhich is optionally monosubstituted to trisubstituted by identical ordifferent substituents, the following being mentioned as substituents:fluorine, chlorine, bromine, nitro, cyclohexyl, straight-chain orbranched alkyl having 1 to 4 carbon atoms, straight-chain or branchedalkoxy having 1 to 3 carbon atoms and alkoxycarbonyl having 1 or 2carbon atoms in the alkoxy part, R^(2') represents straight-chain orbranched alkyl having 1 to 4 carbon atoms, R^(3') and R^(4'), togetherwith the nitrogen atom to which they are bonded, represent a piperidine,morpholine or pyrrolidine radical which is optionally monosubstituted totrisubstituted by identical or different alkyl radicals having 1 to 3carbon atoms.
 11. A substituted aminoketal of the formula according toclaim 8, in whichR^(1') represents the groupings ##STR882## wherein R⁶represents phenyl which in each case is optionally monosubstituted totrisubstituted by identical or different substituents, the followingbeing mentioned as substituents: fluorine, chlorine, bromine, nitro,cyclohexyl, straight-chain or branched alkyl or alkoxy, each having 1 to4 carbon atoms, and alkoxycarbonyl having 1 or 2 carbon atoms in thealkoxy part, R^(2') represents straight-chain or branched alkyl having 1to 4 carbon atoms, and R^(3') and R^(4'), together with the nitrogenatom to which they are bonded, represent the piperidine, morpholine orpyrrolidine radical which is optionally monosubstituted totrisubstituted by identical or different alkyl radicals having 1 to 3carbon atoms.
 12. A compound according to claim 8 wherein such compoundis2-(4-chlorophenoxy-t-butyl)-2-methyl-4-(piperidin-1-ylmethyl)-1,3-dioxolaneof the formula ##STR883## or a physiologically tolerated additionproduct thereof with an acid or metal salt.
 13. A compound according toclaim 8 wherein such compound is2-(2,4-dichlorophenyl-t-butyl)-2-methyl-4-(3-methyl-piperidin-1-ylmethyl)-1,3-dioxolaneof the formula ##STR884## or a physiologically tolerated additionproduct thereof with an acid or metal salt.
 14. A compound according toclaim 8 wherein such compound is2-(2-ethylphenoxy-t-butyl)-2-methyl-4-(3-methyl-piperidin-1-ylmethyl)-1,3-dioxolaneof the formula ##STR885## or a physiologically tolerated additionproduct thereof with an acid or metal salt.
 15. A compound according toclaim 8 wherein such compound is2-(2-ethylphenoxy-t-butyl)-2-methyl-4-(3,5-dimethyl-piperidin-1-ylmethyl)-1,3-dioxolaneof the formula ##STR886## or a physiologically tolerated additionproduct thereof with an acid or metal salt.
 16. A fungicidal compositioncomprising a fungicidally effective amount of a compound or additionproduct thereof according to claim 8 in admixture with a diluent.